How I Tried To Be a Better Startup Weekend Judge

Working with early-stage startups through the Lean Startup Bootcamp and AcceleratorHK, I get to see how lots of people test ideas and build their startups. I also get to see how lots of people want to rush off and build in the beginning, before they know whether their ideas are any good. I’ve also seen a condensed version of this in Startup Weekend. But the truth is, even though I’ve mentored at three Startup Weekends (New York, Hong Kong and Shenzhen) and given pre-Startup Weekend talks, I’ve never been a participant in the event. And now I was to judge at the next Startup Weekend…

So I did the only logical thing in this situation.

I decided to hold my own one-person Startup Weekend to see what it was like. I’ll sum up the experience for you.

It sucked. But I understand even more about why people have such difficulty doing well in these situations.

I had a few rules for how I would participate in this self-made Startup Weekend.

First, I would keep track of how I felt during the two days and would do more of what was enjoyable and less of what was not (sometimes bad choices that I thought participants would be likely to make). I wouldn’t ask for help with the explanation that I’m doing a test, since I think most Startup Weekend participants can’t (or shouldn’t) just ask their friends when they need customer interview subjects and instead should go out and try to find the right people to interview. I’d also have to be developer, designer and business guy without extra help (this one was more about not wanting to drag people in on a holiday weekend). Also, I couldn’t work myself like a real Startup Weekend, since, well, I had other things to do on the weekend. So, overall, this was going to be Startup Weekend-lite, but crazy also.

In terms of being a “good” participant, I was terrible. It was really clear from the start what happens when you let yourself do more of what is fun during what’s supposed to be a competitive learning process. I felt like building and wanted to postpone talking to people. This was made even more difficult for a few reasons.

I had no team. So much of the overall effects of the event come from other people there. Now, as a one-person experimental startup, I had to act all alone. And, I had no one there to encourage me to put the hours in.

I had no other guidance along the way. This actually makes quite a bit of difference. Just being able to talk with someone else about your ideas keeps you from wasting time.

The service I was building was to help people practice their pitches — something I could have found lots of customers for at a Startup Weekend, but not during a normal weekend, especially a holiday weekend. Eleven people I contacted to interview were either unreachable or pushed me off until the following week. According to my rules, I didn’t try to explain that I was working on a self-imposed artificial deadline. Instead, I fell on the unspoken evil of Startup Weekend attendees — the online survey. How else was I to get data so quickly? I received five responses to the survey in the time that I could officially use them (other responses came in afterward).

Further, I was trying to do all of that while also registering a domain (, setting up hosting, email (incorrect MX records led to a couple hours delay), designing a new site and building the two services I was testing. Since I thought that early-stage startups are usually terrible at pitching themselves, I built a service to solve that. The free service I tested was a phone number to call to hear a list of questions you might get when presenting your pitch. The paid service was a grade of you pitching on video and recommendations for how to improve. I built a basic Twilio app for the first (call a phone number and hear questions like “What problem are you solving?” and “How have you tested this idea?”) and relied on PayPal and email for the second.

None of this mattered since I felt uncomfortable about blasting out this fake startup to my contacts so I used a coupon for online ads instead. In the one and a half days I had, I managed to attract one person, I think by accident, to the site. This one person tried neither service.

As Reid Hoffman said, “If you are not embarrassed by the first version of your product, you’ve launched too late.” I was embarrassed but also waited too long for things that didn’t matter. While I spent time designing buttons for the new site (perhaps the most fun of the process) I scrapped all but one of them when I simplified the design.

I also couldn’t truly fulfill the requirement to do much customer development and test the business model (which I could explain, but had no data for since no one chose between the services).

So, suggestions for you include:

  • Form a balanced team
  • Get out of the building and interview potential customers either in-person or online as soon as possible (or set up a schedule starting Friday night latest), Start testing as soon as possible — which is often sooner than you think
  • Remind yourself of the business model, customer development and execution criteria every few hours so you do what has value. Have one person ask “what are we trying to learn and how could we test it faster” every time there’s a new feature suggested
  • Talk to mentors and other teams and get to know people you might work with after the weekend
  • Check out other resources before you begin, such as this Startup Weekend Toolkit

Do all of that and I won’t be too hard on you as a judge.

List of tools and services I used: PHP, CSS, Adobe Illustrator, WordPress, HostGator, GoDaddy, RetailMeNot (for coupons), Bing Ads, Google Analytics, PayPal, Twilio. Also, three glasses of a bottle of Scotch from Steve Messina and a remaining 1/2 bottle of wine from Jeffrey Broer. And here’s something I made afterward to help others after judging at two Startup Weekends.

Filed in: startup programs